Tamsulosin hydrochloride
Synonym(s):(−)-(R)-5-[2-[[2-(o-ethoxy phenoxy)ethyl]amino]propyl]-2-methoxy benzene sulfonamide, monohydrochloride;5-[(2R)-2-[[2-(2-Ethoxyphenoxy)ethyl]amino]propyl]-2-methoxybenzenesulfonamide hydrochloride;TAM;Tamsulosin hydrochloride
- CAS NO.:106463-17-6
- Empirical Formula: C20H29ClN2O5S
- Molecular Weight: 444.97
- MDL number: MFCD00922997
- EINECS: 629-756-5
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-09 19:38:33
What is Tamsulosin hydrochloride ?
Description
Tamsulosin is a potent antagonist of α1-adrenergic receptors (α1-ARs; Ki = 0.229 nM in a radioligand binding assay). It is 3,800-fold selective for α1-ARs over α2-ARs (Ki = 871 nM). Tamsulosin antagonizes norepinephrine-induced contraction of isolated rabbit aorta (pA2 = 10.11) but has no effect on contraction stimulated by histamine, serotonin , angiotensin II , or prostaglandin F2α . In vivo, tamsulosin reverses the pressor effect of phenylephrine (Item Nos. 17205 | 18619) in pithed rats. It reversibly reduces fertility in male rats when administered at a dose of 0.15 mg/kg. Tamsulosin (1-100 μg/kg) also reduces prostatic pressure in a dose-dependent manner with minimal hypotensive effects in anesthetized dogs. Formulations containing tamsulosin have been used for the treatment of benign prostatic hyperplasia.
Chemical properties
White to Off-White Solid
Originator
Contiflo OD,Ranbaxy Laboratories,India
The Uses of Tamsulosin hydrochloride
Specific a1-adrenoceptor antagonist. Used in the treatment of benign prostatic hypertrophy
The Uses of Tamsulosin hydrochloride
Specific α1-adrenoceptor antagonist. Used in the treatment of benign prostatic hypertrophy.
The Uses of Tamsulosin hydrochloride
antineoplastic, alkylating agent
The Uses of Tamsulosin hydrochloride
(R)-Tamsulosin is a specific α1-adrenoceptor antagonist. It is used in the treatment of benign prostatic hypertrophy.
The Uses of Tamsulosin hydrochloride
An α1-adrenoceptor antagonist
Definition
ChEBI: Tamsulosin hydrochloride is a hydrochloride resulting from the reaction of equimolar amounts of tamulosin and hydrogen chloride. It has a role as an alpha-adrenergic antagonist and an antineoplastic agent. It contains a tamsulosin(1+). It is an enantiomer of an ent-tamsulosin hydrochloride.
Manufacturing Process
In 1,000 ml of acetonitrile was suspended 17 g of 5-{2-[2-(2-
ethoxyphenoxy)ethylamino]-1-hydroxy-2-methylethyl}-2-
methoxybenzenesulfonamide hydrochloride and while stirring the suspension,
9 g of thionyl chloride was added dropwise to the suspension at room
temperature, whereby the product first dissolved and then began to crystallize
gradually. After stirring the mixture for two days, the crystals formed were
recovered by filtration, washed with chloroform and dried to provide 15 g of
5-{1-chloro-2-[2-(2-ethoxyphenoxy)ethylamino]-2-methylethyl}-2-
methoxybenzenesulfonamide hydrochloride. Melting point: 197°-200°C.
In methanol was dissolved the 5-{1-chloro-2-[2-(2-
ethoxyphenoxy)ethylamino]ethyl}-2-methoxybenzenesulfonamide
hydrochloride and after adding thereto 10% palladium carbon, dechlorination
was performed under hydrogen stream at normal temperature and pressure.
The palladium carbon was filtered away and the filtrate was concentrated
under reduced pressure to provide the 2-methoxy-5-{2-[2-(2-
ethoxyphenoxy)ethylamino]ethyl}benzenesulfonamide hydrochloride, which
was recrystallized from 120 ml of a mixture of methanol and ethanol (1:4 by
volume ratio) to provide the colorless crystals thereof. The melting point of
the 5-{2-[2-(2-ethoxyphenoxy)ethylamino]-2-methylethyl}-2-
methoxybenzenesulfonamide hydrochloride: 254°-256°C.
Therapeutic Function
Antihypertensive
Mechanism of action
Tamsulosin hydrochloride is an alpha blocker. It works to relax the smooth muscles in your prostate and bladder. This makes it easier to pee and improves the flow of urine.
Side Effects
Common side effects include dizziness, headache, sleeplessness, nausea, blurry vision, and sexual problems. Other side effects may include feeling lightheaded with standing due to changes in blood pressure, and angioedema.
General Description
Tamsulosin hydrochloride is a subtypeselective a1A and a1D adrenoceptor antagonist, which exists in two enantiomeric forms, of which the R-isomer is the pharmaceutically active component. It is used to reduce urinary obstruction and is also involved in relieving the symptoms associated with symptomatic benign prostatic hyperplasia.
Hazard
Moderately toxic by ingestion.
Biological Activity
Selective α 1A -adrenoceptor antagonist (pK i values are 9.97, 9.64 and 8.86 for α 1A , α 1B and α 1D subtypes respectively). Decreases resting maximal urethral pressure with negligable effect on mean arterial blood pressure in vivo .
Biochem/physiol Actions
Tamsulosin is an α1A/1D-adrenoceptor antagonist used as a treatment of benign prostatic hypertrophy (BPH). Its activity as an ? blocker also affects the iris, and has led to complications during cataract surgery, a condition called "floppy iris" syndrome.
storage
Desiccate at RT
Properties of Tamsulosin hydrochloride
Melting point: | 228-230°C |
alpha | D24 -4.0° (c = 0.35 in methanol) |
RTECS | DB2430000 |
storage temp. | 2-8°C |
solubility | DMSO: >10mg/mL |
form | white powder |
color | White to Off-White |
Merck | 14,9049 |
CAS DataBase Reference | 106463-17-6(CAS DataBase Reference) |
Safety information for Tamsulosin hydrochloride
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H302:Acute toxicity,oral |
Precautionary Statement Codes |
P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P270:Do not eat, drink or smoke when using this product. P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. P501:Dispose of contents/container to..… |
Computed Descriptors for Tamsulosin hydrochloride
InChIKey | ZZIZZTHXZRDOFM-XFULWGLBSA-N |
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Synaptics Labs Private Limited
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